Reaction #2042

Reaction equation

triethylamine

Bis(5 -cyclohexyl-4-hydroxy-2-methylphenyl)-3,4-dihydroxyphenylmethane

methanesulfonyl chloride

→

bis(5-cyclohexyl-4-hydroxy-2-methylphenyl)-3,4-dihydroxyphenylmethane

methanesulfonic acid

Solvents

dioxane

dioxane

Conditions

Workup

1. 1
   workup.DISSOLUTIONdissolved
2. 2
   workup.ADDITIONtherein was added dropwise over 40 minutes at a controlled temperature not higher than 35° C
3. 3
   OtherThe precipitating salt was separated by filtration
4. 4
   Otherthe thus recovered reaction product
5. 5
   Washwas washed
6. 6
   Otherdried

Procedure

Bis(5 -cyclohexyl-4-hydroxy-2-methylphenyl)-3,4-dihydroxyphenylmethane(1.0 mole), naphthoquinone-1,2-diazido-5-sulfonyl chloride (2.0 moles) and methanesulfonyl chloride(0.5 moles) were dissolved in dioxane (4,000 g). To the resulting solution, dioxane (1,500 g) having triethylamine (500 g) dissolved therein was added dropwise over 40 minutes at a controlled temperature not higher than 35° C. The precipitating salt was separated by filtration and the thus recovered reaction product was washed and dried to yield a mixed ester of bis(5-cyclohexyl-4-hydroxy-2-methylphenyl)-3,4-dihydroxyphenylmethane with naphthoquinone-1,2-diazido-5-sulfonic acid and methanesulfonic acid; the average degree of esterification was 50% for the quinonediazidosulfonate ester and 12% for the methanesulfonate ester.

Source